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Tandem addition/cyclization for synthesis of 2-aroyl benzofurans and 2-aroyl indoles by carbopalladation of nitriles

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Abstract

The first example of the palladium-catalyzed tandem addition/cyclization of 2-(2-acylphenoxy)acetonitriles with arylboronic acids has been developed, providing a new strategy for the synthesis of 2-aroyl benzofurans with excellent chemoselectivity and wide functional group compatibility. Preliminary mechanistic experiments indicate that this tandem process involves sequential nucleophilic addition generating 2-(2-acylphenoxy)-1-phenylethan-1-one followed by an intramolecular cyclization. This methodology has also been applied to the synthesis of 2-aroyl indoles and the potent CYP19 inhibitor 1-(benzofuran-2-yl(phenyl)methyl)-1H-1,2,4-triazole.

Graphical abstract: Tandem addition/cyclization for synthesis of 2-aroyl benzofurans and 2-aroyl indoles by carbopalladation of nitriles

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Article information


Submitted
07 Nov 2019
Accepted
13 Dec 2019
First published
13 Dec 2019

Org. Biomol. Chem., 2020, Advance Article
Article type
Paper

Tandem addition/cyclization for synthesis of 2-aroyl benzofurans and 2-aroyl indoles by carbopalladation of nitriles

J. Gong, K. Hu, Y. Shao, R. Li, Y. Zhang, M. Hu and J. Chen, Org. Biomol. Chem., 2020, Advance Article , DOI: 10.1039/C9OB02408E

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